Tootsie

The McNay’s “Dressed to Kill” film series seems devoted to cross-dressing, which explains why it includes this romantic dramedy that earned Dustin Hoffman an Oscar nod while donning dowdy drag. Hailing from 1982, Tootsie follows Hoffman as an actor whose annoying personality keeps him out of work until he masquerades as a woman to land a job in a soap opera and finds himself navigating the double standards of gender roles. Sydney Pollack directed and appears in the film alongside Jessica Lange (winning an Oscar), Bill Murray, Geena Davis, Teri Garr and Charles Durning.